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WIN IT ALL Review: Breaking Even

Monday, April 10, 2017 Rob Samuelson

Everybody’s luck changes eventually. That’s what compulsive gamblers always tell themselves, especially perennial losers like Eddie Garrett, played by Jake Johnson in indie filmmaker Joe Swanberg’s latest, Win It All. He’s a grubby, sleepy sort of guy who glides through life with ever-darkening circles beneath his eyes. He parks cars near the Chicago Cubs’ Wrigley Field during the day so he can earn enough petty cash to lose to other desperate and sweaty men at a nightly poker game in the back room of a rundown Chinatown restaurant, which Swanberg bathes in saturated red light and shoots with the fuzzy, grainy look of a 1970s crime picture.

Win It All/IMDb

Michael (José Antonio García), a former “associate” of Eddie’s, breaks into the Eddie’s grimy, barely furnished apartment to offer our grubby hero a deal. Michael’s going away to prison for a while, for about six months or so, and he’s got a black duffel bag that he needs to hide for the duration of his stint in the clink. Don't ask about what's in the bag, don't look inside of it, don't do nothin’ and in six months it'll be a nice payday. Simple, right? Nah. Eddie can't keep his curious paws off of the bag, playfully picking at the zipper, gripping the edges of the mysterious piece of luggage in an attempt to discern what's inside. In a sequence that is the film’s funniest moment, Eddie pulls the zipper down all the way and digs inside, with Johnson uttering a series of increasingly alarmed “On nos” as he pulls out zip ties, a hammer, a frayed rope, and, finally, wads of cash that isn't his. It’s a scene that marries Swanberg’s unflashy camerawork to classic Hollywood sight gags to create one of the most thoroughly cinematic experiences to date in a filmography that is light on such instances. It’s a hilarious kind of tension that leaves viewers with a sense of stakes. If Eddie touches this money, he’s in for a rough ending.

Of course, Eddie does touch the money and he loses, big time. Swanberg and Johnson, who wrote the script together, let this moment sink in as Eddie’s world swirls around him, flushing away any chance of him being able to succeed at the life he tells himself he wants. But that’s when Eddie realizes that his luck actually can change if he changes his idea about what it means to be lucky.

This realization gives the movie its emotional core and its most charming scenes, but it also dumps the comedic tension built in the first half hour. It becomes a redemption tale about the healing powers of supportive friends and forgiving family members. This middle section features a warm turn by comic performer Joe Lo Truglio as Eddie’s brother Ron, who hires Eddie as a laborer at his landscaping business to help him get back on track financially. Keegan-Michael Key appears as Eddie’s addiction sponsor in a small role that taps into Key’s ability to portray insecure maturity. He’s got his life together now and he holds it over Eddie in a way that is both smug and genuine, because not long before was he in Eddie’s spot -- he shows there’s a way out of the hole. Affecting Eddie most of all is the new woman he begins dating, a nurse and single mom named Eva (Aislinn Derbez), who is unwilling to deal with a loser -- she has enough on her plate raising a 7 year old and doesn’t need a man child. This pushes Eddie to realize that he has been living “like a degenerate” and to choose a different life for himself.

This stuff is nice -- but it’s not effective storytelling. It is a series of sweet moments and conflict-free warmth that shows what the beginnings of a balanced life look like. During this interlude Swanberg’s camera returns to his career norm of detaching itself from the action, merely capturing scenes that can meander with too much improvisation. Everything about this is too easy and the movie seems to forget that it’s about a gambler scrambling to come up with the tens of thousands of dollars he owes to a clearly dangerous man. It loses sight of the ticking clock for far too long.

After dawdling for nearly 30 minutes of the total 88-minute runtime, the movie decides to get itself into gear in the third act. Eddie is forced to speed up his repayment timeline in a way he can’t accomplish without returning to gambling. This brings momentum back to the movie, and with momentum comes Swanberg’s directorial control. During the climax, Eddie is out of his scuzzball element at a high-stakes card game in an affluent suburb. Swanberg’s camera patiently circles the players and cuts with a rhythm that begins to reflect the heart that pounds like a piston within the out-of-his-depth Eddie’s chest as he plays for the life he needs, not the one he originally thought he wanted.

When all is said and done, Win It All is a functional, generally satisfying yarn, but it struggles through a mushy middle section. Much like its lead character, it changes its mind about what it wants to be and makes a meaningful change just in the knick of time.

Director: Joe Swanberg
Writers: Jake Johnson, Joe Swanberg
Starring: Jake Johnson, Joe Lo Truglio, Aislinn Derbez, Keegan-Michael Key, José Antonio García
Rating: 3/5 stars
Available on Netflix now

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